Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors
Mapping microviscosity, temperature, and polarity in biosystems is an important capability that can aid in disease detection. This can be achieved using fluorescent sensors based on a green-emitting BODIPY group. However, red fluorescent sensors are desired for convenient imaging of biological sampl...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/1/23 |
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| author | Karolina Maleckaitė Domantas Narkevičius Rugilė Žilėnaitė Jelena Dodonova-Vaitkūnienė Stepas Toliautas Sigitas Tumkevičius Aurimas Vyšniauskas |
| author_facet | Karolina Maleckaitė Domantas Narkevičius Rugilė Žilėnaitė Jelena Dodonova-Vaitkūnienė Stepas Toliautas Sigitas Tumkevičius Aurimas Vyšniauskas |
| author_sort | Karolina Maleckaitė |
| collection | DOAJ |
| description | Mapping microviscosity, temperature, and polarity in biosystems is an important capability that can aid in disease detection. This can be achieved using fluorescent sensors based on a green-emitting BODIPY group. However, red fluorescent sensors are desired for convenient imaging of biological samples. It is known that phenyl substituents in the <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mi mathvariant="sans-serif-italic">β</mi></semantics></math></inline-formula> position of the BODIPY core can shift the fluorescence spectra to longer wavelengths. In this research, we report how electron-withdrawing (EWG) and -donating (EDG) groups can change the spectral and sensory properties of <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mi mathvariant="sans-serif-italic">β</mi></semantics></math></inline-formula>-phenyl-substituted BODIPYs. We present a trifluoromethyl-substituted (EWG) conjugate with moderate temperature sensing properties and a methoxy-substituted (EDG) molecule that could be used as a lifetime-based polarity probe. In this study, we utilise experimental results of steady-state and time-resolved fluorescence, as well as quantum chemical calculations using density functional theory (DFT). We also explain how the energy barrier height (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mi>E</mi><mi>a</mi></msub></semantics></math></inline-formula>) for non-radiative relaxation affects the probe’s sensitivity to temperature and viscosity and provide appropriate <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mi>E</mi><mi>a</mi></msub></semantics></math></inline-formula> ranges for the best possible sensitivity to viscosity and temperature. |
| first_indexed | 2024-03-10T03:32:07Z |
| format | Article |
| id | doaj.art-ac72a46b89c34b07b4a476f83d479a39 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:32:07Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ac72a46b89c34b07b4a476f83d479a392023-11-23T11:55:27ZengMDPI AGMolecules1420-30492021-12-012712310.3390/molecules27010023Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular RotorsKarolina Maleckaitė0Domantas Narkevičius1Rugilė Žilėnaitė2Jelena Dodonova-Vaitkūnienė3Stepas Toliautas4Sigitas Tumkevičius5Aurimas Vyšniauskas6Center of Physical Sciences and Technology, Saulėtekio av. 3, LT-10257 Vilnius, LithuaniaInstitute of Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, Naugarduko str. 24, LT-03225 Vilnius, LithuaniaInstitute of Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, Naugarduko str. 24, LT-03225 Vilnius, LithuaniaInstitute of Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, Naugarduko str. 24, LT-03225 Vilnius, LithuaniaInstitute of Chemical Physics, Faculty of Physics, Vilnius University, Saulėtekio av. 9-III, LT-10222 Vilnius, LithuaniaInstitute of Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, Naugarduko str. 24, LT-03225 Vilnius, LithuaniaCenter of Physical Sciences and Technology, Saulėtekio av. 3, LT-10257 Vilnius, LithuaniaMapping microviscosity, temperature, and polarity in biosystems is an important capability that can aid in disease detection. This can be achieved using fluorescent sensors based on a green-emitting BODIPY group. However, red fluorescent sensors are desired for convenient imaging of biological samples. It is known that phenyl substituents in the <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mi mathvariant="sans-serif-italic">β</mi></semantics></math></inline-formula> position of the BODIPY core can shift the fluorescence spectra to longer wavelengths. In this research, we report how electron-withdrawing (EWG) and -donating (EDG) groups can change the spectral and sensory properties of <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mi mathvariant="sans-serif-italic">β</mi></semantics></math></inline-formula>-phenyl-substituted BODIPYs. We present a trifluoromethyl-substituted (EWG) conjugate with moderate temperature sensing properties and a methoxy-substituted (EDG) molecule that could be used as a lifetime-based polarity probe. In this study, we utilise experimental results of steady-state and time-resolved fluorescence, as well as quantum chemical calculations using density functional theory (DFT). We also explain how the energy barrier height (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mi>E</mi><mi>a</mi></msub></semantics></math></inline-formula>) for non-radiative relaxation affects the probe’s sensitivity to temperature and viscosity and provide appropriate <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mi>E</mi><mi>a</mi></msub></semantics></math></inline-formula> ranges for the best possible sensitivity to viscosity and temperature.https://www.mdpi.com/1420-3049/27/1/23fluorescent probesphotophysicsmolecular rotorsmicroviscositypolarity sensing |
| spellingShingle | Karolina Maleckaitė Domantas Narkevičius Rugilė Žilėnaitė Jelena Dodonova-Vaitkūnienė Stepas Toliautas Sigitas Tumkevičius Aurimas Vyšniauskas Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors Molecules fluorescent probes photophysics molecular rotors microviscosity polarity sensing |
| title | Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors |
| title_full | Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors |
| title_fullStr | Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors |
| title_full_unstemmed | Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors |
| title_short | Give or Take: Effects of Electron-Accepting/-Withdrawing Groups in Red-Fluorescent BODIPY Molecular Rotors |
| title_sort | give or take effects of electron accepting withdrawing groups in red fluorescent bodipy molecular rotors |
| topic | fluorescent probes photophysics molecular rotors microviscosity polarity sensing |
| url | https://www.mdpi.com/1420-3049/27/1/23 |
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